Metal-free three-component assemblies of anilines, α-keto acids and alkyl lactates for quinoline synthesis and their anti-inflammatory activity

Huang, Lingxia; Yang, Lei; Wan, Jie‐Ping; Zhou, Liyun; Liu, Yunyun; Hao, Guifeng

doi:10.1039/d2ob00661h

Cited by 12 publications

(6 citation statements)

References 73 publications

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“…2-Substituted quinoline motifs are prevalent in natural products and pharmaceuticals, many of which demonstrate potent biological activities (Scheme 1a). [1][2][3][4][5][6][7] The synthesis of these privileged scaffolds has thus drawn a lot of attention. The radical cascade cyclization of o-arylphenylisocyanides or o-vinylphenylisocyanides represents a convenient methodology for accessing substituted quinolines or phenanthridines because one can install a pyridine ring and its ortho substituent in one step (Scheme 1b).…”

Section: Introductionmentioning

confidence: 99%

Catalyst-free aerobic radical cascade reactions of o-vinylphenylisocyanides with thiols to access 2-thio-substituted quinolines

Wang

Liu

et al. 2022

Org. Chem. Front.

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Section: Introductionmentioning

confidence: 99%

Catalyst-free aerobic radical cascade reactions of o-vinylphenylisocyanides with thiols to access 2-thio-substituted quinolines

Wang

Liu

et al. 2022

Org. Chem. Front.

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“…Huang and his co-worker developed the synthesis of quinoline derivatives 553 from anilines 3, α-keto acids 551 and alkyl lactates 552 via MCR (Scheme 106). [125] A series of quinoline derivatives were synthesized in presence of p-toluene sulfonic acid (p-TSA) and tert-butyl peroxybenzoate (TBPB) via formation of new C=C double, CÀ C single and C=N bonds without producing any side product. Patel and his group demonstrate the microwave-assisted MCR for the synthesis of pyrimido [4,5-b]quinoline derivatives 561 by using aromatic aldehydes 1, 6-amino-2,4-dimethoxypyrimidine and dimedone in acetic acid medium (Scheme 107).…”

Section: Synthesis Of Pyridines and Quinolinesmentioning

confidence: 99%

“…Huang and his co‐worker developed the synthesis of quinoline derivatives 553 from anilines 3 , α‐keto acids 551 and alkyl lactates 552 via MCR (Scheme 106). [125] …”

Section: Six‐membered Heterocyclic Compoundsmentioning

confidence: 99%

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

et al. 2023

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Multicomponent reactions (MCRs) have emerged as powerful tools in synthetic chemistry for the efficient synthesis of diverse molecular scaffolds, particularly nitrogen‐containing heterocycles. Despite their numerous advantages, the use of transition metal catalysts or additives in MCRs can present limitations due to cost, toxicity, and environmental concerns. In recent years, there has been a growing interest in transition metal‐free MCRs for the synthesis of N‐heterocyclic compounds. This review provides a comprehensive and concise overview of the recent advancements in transition metal‐free MCRs for the synthesis of valuable N‐heterocycles over the past five years. The review is systematically organized, categorizing the discussed MCRs based on the size of the heterocyclic ring and the number of nitrogen atoms. Only MCRs that result in the formation of heterocyclic rings containing at least one nitrogen atom are included, while the derivatization of N‐heterocycles using transition metal‐free MCRs falls outside the scope of this review. By highlighting the recent developments in this field, this review aims to showcase the potential and significance of transition metal‐free MCRs as sustainable and efficient strategies for accessing N‐heterocyclic compounds. The elimination of transition metals not only simplifies the reaction conditions but also contributes to greener and more environmentally friendly synthetic approaches. This review serves as a valuable resource for researchers interested in the design and application of transition metal‐free MCRs in the synthesis of nitrogen‐containing heterocycles.

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“…In addition, a number of commercial retail drugs contain quinoline skeletons, such as Lenvima, Tafenoquine, Chiniofon, and Clioquinol . Owing to their increasing importance, more and more attention has been devoted to the synthesis of quinoline derivatives . The most traditional protocols for quinoline ring construction include Niementowski, Skraup, Doebner–von Miller, Pfitzinger, and Friedländer syntheses .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Indenoquinolinones and 2-Substituted Quinolines via [4 + 2] Cycloaddition Reaction

et al. 2022

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We have reported a metal-free protocol for the synthesis of indenoquinolinones and 2-substituted quinolines via [4 + 2] cycloaddition reaction using readily available 2-aminobenzaldehydes and ketones as starting materials. Different quinoline derivatives can be selectively synthesized by changing the type of ketones. O 2 and dimethyl sulfoxide (DMSO) as co-oxidants play an important role in the synthesis of indenoquinolinones. This condensation/oxidation strategy involves the formation of C−N, C−C, and C−O bonds, with the advantages of high yields and a broad substrate range.

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Metal-free three-component assemblies of anilines, α-keto acids and alkyl lactates for quinoline synthesis and their anti-inflammatory activity

Abstract: A new three-component method for the synthesis of 2,4-disubstituted quinolines via the three-component reactions of anilines, α-keto carboxylic acids and alkyl lactates is reported. The reactions proceed in the presence...

Cited by 12 publications

References 73 publications

Catalyst-free aerobic radical cascade reactions of o-vinylphenylisocyanides with thiols to access 2-thio-substituted quinolines

Catalyst-free aerobic radical cascade reactions of o-vinylphenylisocyanides with thiols to access 2-thio-substituted quinolines

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Synthesis of Indenoquinolinones and 2-Substituted Quinolines via [4 + 2] Cycloaddition Reaction

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